#------------------------------------------------------------------------------
#$Date: 2020-11-04 03:24:20 +0200 (Wed, 04 Nov 2020) $
#$Revision: 258711 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/52/4135292.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4135292
loop_
_publ_author_name
'Ni, Hangcheng'
'Lu, Zhenpin'
'Xie, Zuowei'
_publ_section_title
;
 Transition-Metal-Free Cross-Coupling Reaction of Iodocarboranes with
 Terminal Alkynes Enabled by UV Light: Synthesis of
 1-Alkynyl-o-Carboranes and Carborane-Fused Cyclics.
;
_journal_issue                   43
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18661
_journal_page_last               18667
_journal_paper_doi               10.1021/jacs.0c08652
_journal_volume                  142
_journal_year                    2020
_chemical_formula_sum            'C15 H26 B10 O'
_chemical_formula_weight         330.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3162(5)
_cell_length_b                   7.2812(3)
_cell_length_c                   19.0278(7)
_cell_measurement_reflns_used    135
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     1983.44(13)
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            33890
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.242
_diffrn_reflns_theta_min         1.780
_exptl_absorpt_coefficient_mu    0.058
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6856
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1953
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0564
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0939P)²+0.5955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1589
_refine_ls_wR_factor_ref         0.1723
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1630
_reflns_number_total             1953
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            10Bb.cif
_cod_data_source_block           10Bb
_cod_depositor_comments
'Adding full bibliography for 4135283--4135293.cif.'
_cod_database_code               4135292
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.977
_shelx_estimated_absorpt_t_max   0.983
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.81642(15) 0.2500 0.39421(10) 0.0822(7) Uani 1 2 d S T P . .
C1 C 0.93927(14) 0.2500 0.67380(11) 0.0407(5) Uani 1 2 d S T P . .
C2 C 1.05185(14) 0.2500 0.68406(11) 0.0435(5) Uani 1 2 d S T P . .
C11 C 0.90657(15) 0.2500 0.59973(11) 0.0425(5) Uani 1 2 d S T P . .
C12 C 0.81179(16) 0.2500 0.58637(14) 0.0541(6) Uani 1 2 d S T P . .
H12A H 0.7699 0.2500 0.6237 0.065 Uiso 1 2 calc R U P . .
C13 C 0.77812(18) 0.2500 0.51819(16) 0.0620(7) Uani 1 2 d S T P . .
H13A H 0.7141 0.2500 0.5097 0.074 Uiso 1 2 calc R U P . .
C14 C 0.8401(2) 0.2500 0.46332(14) 0.0575(7) Uani 1 2 d S T P . .
C15 C 0.93479(18) 0.2500 0.47616(12) 0.0510(6) Uani 1 2 d S T P . .
H15A H 0.9759 0.2500 0.4383 0.061 Uiso 1 2 calc R U P . .
C16 C 0.97042(16) 0.2500 0.54378(11) 0.0425(5) Uani 1 2 d S T P . .
C17 C 1.07258(15) 0.2500 0.55503(11) 0.0432(5) Uani 1 2 d S T P . .
C18 C 1.10770(15) 0.2500 0.61939(11) 0.0484(6) Uani 1 2 d S T P . .
H18A H 1.1724 0.2500 0.6239 0.058 Uiso 1 2 calc R U P . .
C19 C 0.7208(3) 0.2500 0.3760(2) 0.0992(13) Uani 1 2 d S T P . .
H19A H 0.7146 0.2500 0.3258 0.149 Uiso 1 2 calc R U P . .
H19B H 0.6914 0.1423 0.3950 0.149 Uiso 0.5 1 calc R U P . .
H19C H 0.6914 0.3577 0.3950 0.149 Uiso 0.5 1 calc R U P . .
C20 C 1.13547(17) 0.2500 0.49143(12) 0.0505(6) Uani 1 2 d S T P . .
H20A H 1.1207 0.1427 0.4633 0.061 Uiso 0.5 1 calc R U P . .
H20B H 1.1207 0.3573 0.4633 0.061 Uiso 0.5 1 calc R U P . .
C21 C 1.23892(16) 0.2500 0.50555(13) 0.0541(6) Uani 1 2 d S T P . .
H21A H 1.2544 0.1424 0.5333 0.065 Uiso 0.5 1 calc R U P . .
H21B H 1.2544 0.3576 0.5333 0.065 Uiso 0.5 1 calc R U P . .
C22 C 1.2985(2) 0.2500 0.43919(16) 0.0781(9) Uani 1 2 d S T P . .
H22A H 1.2837 0.1423 0.4114 0.094 Uiso 0.5 1 calc R U P . .
H22B H 1.2837 0.3577 0.4114 0.094 Uiso 0.5 1 calc R U P . .
C23 C 1.4014(3) 0.2500 0.4559(2) 0.1315(18) Uani 1 2 d S T P . .
H23A H 1.4366 0.2500 0.4130 0.197 Uiso 1 2 calc R U P . .
H23B H 1.4166 0.3577 0.4827 0.197 Uiso 0.5 1 calc R U P . .
H23C H 1.4166 0.1423 0.4827 0.197 Uiso 0.5 1 calc R U P . .
B3 B 0.88645(13) 0.1280(3) 0.73925(10) 0.0570(6) Uani 1 1 d . . . . .
H3 H 0.8215 0.0491 0.7325 0.068 Uiso 1 1 calc R U . . .
B4 B 0.99180(13) 0.0504(3) 0.70319(10) 0.0509(5) Uani 1 1 d . . . . .
H4 H 0.9964 -0.0782 0.6731 0.061 Uiso 1 1 calc R U . . .
B5 B 0.9124(2) 0.2500 0.81695(15) 0.0666(9) Uani 1 2 d S T P . .
H5 H 0.8643 0.2500 0.8620 0.080 Uiso 1 2 calc R U P . .
B6 B 0.97777(15) 0.0531(4) 0.79470(11) 0.0653(6) Uani 1 1 d . . . . .
H6 H 0.9730 -0.0746 0.8254 0.078 Uiso 1 1 calc R U . . .
B7 B 1.08356(14) 0.1280(4) 0.75663(9) 0.0603(6) Uani 1 1 d . . . . .
H7 H 1.1488 0.0491 0.7612 0.072 Uiso 1 1 calc R U . . .
B8 B 1.0348(2) 0.2500 0.82812(15) 0.0667(9) Uani 1 2 d S T P . .
H8 H 1.0677 0.2500 0.8804 0.080 Uiso 1 2 calc R U P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O1 C19 118.6(3) . . ?
C11 C1 C2 115.28(17) . . ?
C11 C1 B3 123.57(14) . . ?
C2 C1 B3 110.61(14) . . ?
C11 C1 B3 123.57(14) . 7_565 ?
C2 C1 B3 110.61(14) . 7_565 ?
B3 C1 B3 62.75(17) . 7_565 ?
C11 C1 B4 116.36(10) . 7_565 ?
C2 C1 B4 61.92(9) . 7_565 ?
B3 C1 B4 113.21(15) . 7_565 ?
B3 C1 B4 61.26(11) 7_565 7_565 ?
C11 C1 B4 116.36(10) . . ?
C2 C1 B4 61.93(9) . . ?
B3 C1 B4 61.26(11) . . ?
B3 C1 B4 113.21(15) 7_565 . ?
B4 C1 B4 114.37(17) 7_565 . ?
C18 C2 C1 116.10(17) . . ?
C18 C2 B7 122.31(14) . 7_565 ?
C1 C2 B7 111.23(14) . 7_565 ?
C18 C2 B7 122.31(14) . . ?
C1 C2 B7 111.23(14) . . ?
B7 C2 B7 62.87(19) 7_565 . ?
C18 C2 B4 116.60(10) . 7_565 ?
C1 C2 B4 62.05(9) . 7_565 ?
B7 C2 B4 61.51(11) 7_565 7_565 ?
B7 C2 B4 113.62(15) . 7_565 ?
C18 C2 B4 116.60(10) . . ?
C1 C2 B4 62.05(9) . . ?
B7 C2 B4 113.62(15) 7_565 . ?
B7 C2 B4 61.51(11) . . ?
B4 C2 B4 114.57(17) 7_565 . ?
C12 C11 C16 120.0(2) . . ?
C12 C11 C1 119.0(2) . . ?
C16 C11 C1 120.98(19) . . ?
C11 C12 C13 121.0(2) . . ?
C14 C13 C12 119.3(2) . . ?
O1 C14 C13 125.2(2) . . ?
O1 C14 C15 114.6(3) . . ?
C13 C14 C15 120.1(2) . . ?
C14 C15 C16 121.8(2) . . ?
C15 C16 C11 117.7(2) . . ?
C15 C16 C17 120.0(2) . . ?
C11 C16 C17 122.32(19) . . ?
C18 C17 C16 120.66(19) . . ?
C18 C17 C20 121.0(2) . . ?
C16 C17 C20 118.32(19) . . ?
C17 C18 C2 124.7(2) . . ?
C21 C20 C17 116.4(2) . . ?
C20 C21 C22 113.8(2) . . ?
C23 C22 C21 111.9(3) . . ?
C1 B3 B4 60.01(10) . . ?
C1 B3 B5 104.85(15) . . ?
B4 B3 B5 108.05(16) . . ?
C1 B3 B6 105.59(14) . . ?
B4 B3 B6 59.79(11) . . ?
B5 B3 B6 59.95(13) . . ?
C1 B3 B3 58.63(9) . 7_565 ?
B4 B3 B3 108.83(10) . 7_565 ?
B5 B3 B3 59.76(9) . 7_565 ?
B6 B3 B3 107.98(12) . 7_565 ?
C2 B4 C1 56.03(10) . . ?
C2 B4 B3 103.88(14) . . ?
C1 B4 B3 58.73(11) . . ?
C2 B4 B6 104.88(15) . . ?
C1 B4 B6 105.19(15) . . ?
B3 B4 B6 60.55(11) . . ?
C2 B4 B7 58.58(12) . . ?
C1 B4 B7 104.03(15) . . ?
B3 B4 B7 108.30(15) . . ?
B6 B4 B7 60.43(11) . . ?
B6 B5 B6 108.7(2) . 7_565 ?
B6 B5 B3 108.65(17) . 7_565 ?
B6 B5 B3 60.08(12) 7_565 7_565 ?
B6 B5 B3 60.08(12) . . ?
B6 B5 B3 108.64(17) 7_565 . ?
B3 B5 B3 60.47(18) 7_565 . ?
B6 B5 B8 60.12(12) . . ?
B6 B5 B8 60.12(12) 7_565 . ?
B3 B5 B8 108.03(17) 7_565 . ?
B3 B5 B8 108.03(17) . . ?
B4 B6 B5 107.97(16) . . ?
B4 B6 B7 59.84(11) . . ?
B5 B6 B7 107.64(18) . . ?
B4 B6 B3 59.66(11) . . ?
B5 B6 B3 59.97(14) . . ?
B7 B6 B3 107.14(14) . . ?
B4 B6 B8 108.27(16) . . ?
B5 B6 B8 60.00(15) . . ?
B7 B6 B8 60.05(15) . . ?
B3 B6 B8 107.85(18) . . ?
C2 B7 B4 59.91(10) . . ?
C2 B7 B6 105.37(14) . . ?
B4 B7 B6 59.74(12) . . ?
C2 B7 B8 104.85(16) . . ?
B4 B7 B8 108.19(16) . . ?
B6 B7 B8 60.06(13) . . ?
C2 B7 B7 58.56(9) . 7_565 ?
B4 B7 B7 108.78(11) . 7_565 ?
B6 B7 B7 107.99(12) . 7_565 ?
B8 B7 B7 59.83(9) . 7_565 ?
B5 B8 B7 107.41(18) . . ?
B5 B8 B7 107.40(18) . 7_565 ?
B7 B8 B7 60.33(18) . 7_565 ?
B5 B8 B6 59.88(12) . 7_565 ?
B7 B8 B6 108.24(17) . 7_565 ?
B7 B8 B6 59.88(12) 7_565 7_565 ?
B5 B8 B6 59.88(12) . . ?
B7 B8 B6 59.88(12) . . ?
B7 B8 B6 108.24(17) 7_565 . ?
B6 B8 B6 108.3(2) 7_565 . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C14 1.358(3) . ?
O1 C19 1.412(4) . ?
C1 C11 1.485(3) . ?
C1 C2 1.623(3) . ?
C1 B3 1.706(2) . ?
C1 B3 1.707(2) 7_565 ?
C1 B4 1.729(2) 7_565 ?
C1 B4 1.729(2) . ?
C2 C18 1.468(3) . ?
C2 B7 1.704(3) 7_565 ?
C2 B7 1.704(3) . ?
C2 B4 1.727(2) 7_565 ?
C2 B4 1.727(2) . ?
C11 C12 1.381(3) . ?
C11 C16 1.403(3) . ?
C12 C13 1.384(4) . ?
C13 C14 1.370(4) . ?
C14 C15 1.378(4) . ?
C15 C16 1.384(3) . ?
C16 C17 1.478(3) . ?
C17 C18 1.324(3) . ?
C17 C20 1.508(3) . ?
C20 C21 1.505(3) . ?
C21 C22 1.524(3) . ?
C22 C23 1.506(5) . ?
B3 B4 1.751(3) . ?
B3 B5 1.764(3) . ?
B3 B6 1.766(3) . ?
B3 B3 1.777(5) 7_565 ?
B4 B6 1.753(3) . ?
B4 B7 1.755(3) . ?
B5 B6 1.764(3) . ?
B5 B6 1.764(3) 7_565 ?
B5 B3 1.764(3) 7_565 ?
B5 B8 1.766(4) . ?
B6 B7 1.765(3) . ?
B6 B8 1.768(3) . ?
B7 B8 1.768(3) . ?
B7 B7 1.777(5) 7_565 ?
B8 B7 1.768(3) 7_565 ?
B8 B6 1.768(3) 7_565 ?
